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Articles • J. Braz. Chem. Soc. 20 (8) • 2009 • https://doi.org/10.1590/S0103-50532009000800014   copy

Synthesis of α- and β-lapachone derivatives from hetero diels-alder trapping of alkyl and aryl o-quinone methides

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Methylene and aryl o-quinone methides (o-QMs) generated by Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with formaldehyde and arylaldehydes, undergo facile hetero Diels-Alder reaction with some substituted styrenes (as dienophiles) in aqueous ethanol media providing derivatives of α- and β-lapachone.

o-Quinone methides; Knoevenagel condensation; Hetero Diels-Alder; Lapachones

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